Cesium carbonate → HCID 18477086, compound

HRID 2188218Notes

Reaction equation

HRID 2188218 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[O:13]([CH2:20][CH2:21]Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O.C(OCC)C>[O:13]([CH2:20][CH2:21][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenone

Product 1

HCID 18477086HCID 18477086, compoundYield 73.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-hydroxy-3,4-dihydro-2H-naphthalen-1-one (2.5 g), 2-phenoxyethyl bromide (3.4 g) and cesium carbonate (5.5 g) were stirred in N,N-dimethylformamide (15 cm3) and heated at 100° C. for 2.5 h. The reaction mixture was allowed to cool to room temperature and then diluted with water (150 cm3). The aqueous mixture was extracted with ethyl acetate (2×50 cm3) and the organic extracts were washed with aqueous sodium hydroxide (1 M, 50 cm3), water (50 cm3) and then hydrochloric acid (2 M, 50 cm3). The organic extracts were dried (Na2SO4) and the solvent removed under reduced pressure to afford the crude product which was suspended in diethyl ether and filtered to yield the title compound (3.2 g).

Workup

  1. temperatureto cool to room temperature
  2. extractionThe aqueous mixture was extracted with ethyl acetate (2×50 cm3)
  3. washthe organic extracts were washed with aqueous sodium hydroxide (1 M, 50 cm3), water (50 cm3)
  4. dry with materialThe organic extracts were dried (Na2SO4)
  5. customthe solvent removed under reduced pressure
  6. customto afford the crude product which
  7. filtrationfiltered

Sources & evidence

ORD record
ord-f9db96bd9941475a87cfea03a2c98cb0
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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